4-Nitrobenzoic Acid → 4-Nitroprocainamide

A mixture of 4-nitrobenzoic acid (2.00 g, 11.9 mmol), N,N-diethylethylene diamine (1.53 g, 13.16 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.74 g, 14.35 mmol), and 1-hydroxybenzotriazole hydrate (2.19 g, 14.35 mmol) in 15 mL DMF was stirred at room temperature for 4 hours. The mixture was diluted with dichloromethane (100 mL) and washed with aqueous saturated sodium bicarbonate solution (50 mL). The aqueous layer was re-extracted with dichloromethane (2×50 mL) and the combined organic solutions were dried (Na2SO4), filtered and evaporated under reduced pressure. The crude mixture was purified on silica gel column to provide N-(2-(diethylamino)-ethyl)-4-nitrobenzamide as an amber colored oil (2.2 g 69%).

1. washwashed with aqueous saturated sodium bicarbonate solution (50 mL)
2. extractionThe aqueous layer was re-extracted with dichloromethane (2×50 mL)
3. dry with materialthe combined organic solutions were dried (Na2SO4)
4. filtrationfiltered
5. customevaporated under reduced pressure
6. customThe crude mixture was purified on silica gel column

ORD record

ord-fe6e1669a2c4419988f5ea3b34bad979

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07692005B2